Back in college, Sanket and I would hang out in bars and try to talk to women, but I was horrible at it. Nobody would talk to me for more than 30 seconds and every woman would laugh at all his jokes for what seemed like hours. Even decades later I think they are still laughing at his jokes.

One time he turned to me, “the girls are getting bored when you talk. Your stories go on too long. From now on, you need to leave out every other sentence when you tell a story.” We were both undergrads in Computer Science.

I haven’t seen him since, but that’s the most important writing (and communicating) advice I ever got.

33 other tips to be a better writer.

– Write whatever you want. Then take out the first paragraph and last paragraph. Here’s the funny thing about this rule. It’s sort of like knowing the future. You still can’t change it. In other words, even if you know this rule and write the article, the article will still be better if you take out the first paragraph and the last paragraph.

– Take a huge bowel movement every day. And you won’t see that on any other list on how to be a better writer. If your body doesn’t flow then your brain won’t flow. Eat more fruit if you have to.

– Bleed in the first line. We’re all human. A computer can win Jeopardy but still not write a novel. You want people to relate to you, then you have to be human. Penelope Trunk started a post a few weeks ago: “I smashed a lamp over my head. There was blood everywhere. And glass. And I took a picture.” That’s real bleeding. My wife recently put up a post where the first line was so painful she had to take it down. Too many people were crying.

Write a lot. I spent the entire 90s writing bad fiction. 5 bad novels. Dozens of bad stories. But I learned to handle massive rejection. And how to put two words together. In my head, I won the pulitzer prize. But in my hand, over 100 rejection letters.

Read a lot. You can’t write without first reading. A lot. When I was writing five bad novels in a row I would read all day long whenever I wasn’t writing (I had a job as a programmer, which I would do for about five minutes a day because my programs all worked and I just had to “maintain” them). I read everything I could get my hands on.

Read before you write. Before I write every day I spend 30-60 minutes reading high quality short stories poetry, or essays. Books by Denis Johnson, Miranda July, David Foster Wallace, Ariel Leve, William Vollmann, Raymond Carver, etc. All of the writers are in the top 1/1000 of 1% of writers. It has to be at that level or else it won’t lift up your writing at all.

Coffee. I go through three cups at least before I even begin to write. No coffee, no creativity.

Break the laws of physics. There’s no time in text. Nothing has to go in order. Don’t make it nonsense. But don’t be beholden to the laws of physics.

Be Honest. Tell people the stuff they all think but nobody ever says. Some people will be angry you let out the secret. But most people will be grateful. Else you aren’t delivering value. Be the little boy in the Emperor Wears No Clothes. If you can’t do this, don’t write.

Don’t Hurt Anyone. This goes against the above rule. But I never like to hurt people. And I don’t respect people who get pageviews by breaking this rule. Don’t be a bad guy.

Don’t be afraid of what people think. For each single person you worry about, deduct 1% in quality from your writing. Everyone has deductions. I have to deduct about 10% right off the top. Maybe there’s 10 people I’m worried about. Some of them are evil people. Some of them are people I just don’t want to offend. So my writing is only about 90% of what it could be. But I think most people write at about 20% of what it could be. Believe it or not, clients, customers, friends, family, will love you more if you are honest with them. So we all have our boundaries. But try this: for the next 10 things you write, tell people something that nobody knows about you.

Be opinionated. Most people I know have strong opinions about at least one or two things. Write about those. Nobody cares about all the things you don’t have strong opinions on. Barry Ritholz told me the other day he doesn’t start writing until he’s angry about something. That’s one approach. Barry and I have had some great writing fights because sometimes we’ve been angry at each other.

Have a shocking title. I blew it the other day. I wanted to title this piece: “How I torture women”but I settled for “I’m guilty of torture”. Don’t forget that you are competing against a trillion other pieces of content out there. So you need a title to draw people in. Else you lose.

Steal. I don’t quite mean it literally. But if you know a topic gets pageviews (and you aren’t hurting anyone) than steal it, no matter who’s written about it or how many times you’ve written about it before. “How I Screwed Yasser Arafat out of $2mm” was able to nicely piggyback off of how amazingly popular Yasser Arafat is.

Make people cry. If you’ve ever been in love, you know how to cry. Bring readers to that moment when they were a child, and all of life was in front of them, except for that one bittersweet moment when everything began to change. If only that one moment could’ve lasted forever. Please let me go back in time right now to that moment. But now it’s gone.

Relate to people. The past decade has totally sucked. For everyone. The country has been in post-traumatic stress syndrome since 9/11 and 2008 only made it worse. I’ve gone broke a few times during the decade, had a divorce, lost friendships, and have only survived (barely) by being persistent and knowing I had two kids to take care of, and loneliness to fight. Nobody’s perfect. We’re all trying. Show people how you are trying and struggling. Nobody expects you to be a superhero.

Time heals all wounds. Everyone has experiences they don’t want to write about. But with enough time, its ok. My New Year’s Resolution of 1995 is pretty embarrassing. But whatever. Its 16 years ago.. The longer back you go, the less you have to worry about what people think.

Risk. Notice that almost all of these rules are about where the boundaries are. Most people play it too safe. When you are really risking something and the reader senses that (and they WILL sense it), then you know you are in good territory. If you aren’t risking something, then I’m moving on. I know I’m on the right track if after I post something someone tweets, “OMFG”.

Be funny. You can be all of the above and be funny at the same time. When I went to India I was brutalized by my first few yoga classes (actually every yoga class). And I was intimidated by everyone around me. They were like yoga superheroes and I felt like a fraud around them. So I cried, and hopefully people laughed [This post got lots of comments here at Elephant!]. It was also a case where I didn’t have to dig into my past but I had an experience that was happening to me right then. How do you be funny? First rule of funny: ugly people are funny. I’m naturally ugly so its easy. Make yourself as ugly as possible. Nobody wants to read that you are beautiful and doing great in life.

The last line needs to go BOOM! Your article is meaningless unless the last line KILLS. Read the book of short stories “Jesus’ Son” by Denis Johnson. It’s the only way to learn how to do a last line. The last line should take you all the way back to the first line and then “BOOM!”

Use a lot of periods. Forget commas and semicolons. A period makes people pause. Your sentences should be strong enough that you want people to pause and think about it. This will also make your sentences shorter. Short sentences are good.

Write every day. This is a must. Writing is spiritual practice. You are diving inside of yourself and cleaning out the toxins. If you don’t do it every day, you lose the ability. If you do it every day, then slowly you find out where all the toxins are. And the cleaning can begin.

Write with the same voice you talk in. You’ve spent your whole life learning how to communicate with that voice. Why change it when you communicate with text?

Deliver value with every sentence. Even on a tweet or Facebook status update. Deliver poetry and value with ever word. Else, be quiet.

Take what everyone thinks and explore the opposite. Don’t disagree just to disagree. But explore. Turn the world upside down. Guess what? There are people living in China. Plenty of times you’ll find value where nobody else did.

Have lots of ideas. I discuss this in “How to be the Luckiest Man Alive” in the Daily Practice section. Your idea muscle atrophies within days if you don’t exercise it. Then what do you do? You need to exercise it every day until it hurts. Else no ideas.

Sleep eight hours a day. Go to sleep before 9pm at least 4 days a week. And stretch while taking deep breaths before you write. We supposedly use only 5% of our brain. You need to use 6% at least to write better than everyone else. So make sure your brain is getting as much healthy oxygen as possible. Too many people waste valuable writing or resting time by chattering until all hours of the night.

Don’t write if you’re upset at someone. Then the person you are upset at becomes your audience. You want to love and flirt with your audience so they can love you back.

Use “said” instead of any other word. Don’t use “he suggested” or “he bellowed.” Just “he said.” We’ll figure it out if he suggested something.

Paint. Or draw. Keep exercising other creative muscles.

Let it sleep. Whatever you are working on, sleep on it. Then wake up, stretch, coffee, read, and look again. Rewrite. Take out every other sentence.

Then take out every other sentence again. Or something like that.

Sanket didn’t want to go to grad school after we graduated. He had another plan. Lets go to Thailand, he said. And become monks in a Buddhist monastery for a year. We can date Thai women whenever we aren’t begging for food, he said. It will be great and we’ll get life experience.

It sounded good to me.

But then he got accepted to the University of Wisconsin and got a PhD. Now he lives in India and works for Oracle. And as for me, I don’t know what the hell happened to me.

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LOVE Denis Johnson – especially Jesus' Son – and was thrilled to see him mentioned in this peice! what a great writer! And DFW, too. Thanks for the writing tips! Do you like Rick Moody or Paul Auster??

Just discovered this article- a little late for the train – but oh wow, THANK YOU!! I have a constant urge to write about my magical life experiences, and inspire people, but I get distracted by life! These tips have lit the fire inside once again! Keep up your awesome work, and happiest of new years!

[…] I’ll get rejected today’, I thought as I licked the envelope containing another letter to yet another magazine. ‘Of course they’ll choose someone else’, I mused as I walked away from an interview, kicking […]

A great list – assuming someone knows how to write. If not, taking a dump isn't going to help (I've heard editors say that all writers are basically full of sh*t). But for *real writers*, your advice is candid, inspiring, and eminently useful. Thanks!

From my experience as an (as of yet unpublished) writer, I find that nearly everything you said (noticed how I did not say "suggested") has worked wonderfully for me and my works. Wonderful post! Thank you so much!

Reading to become a better writer is fairly basic. It takes decades of voracious reading to learn how to write. There are no short cuts.

I would take issue with the idea that shorter sentences are necessarily better. Nobody really needs to write like Kant, but the length and structure of the sentence corresponds to the concept being conveyed. More complex and sophisticated concepts require longer and more sophisticated sentences and punctuation to convey. The problem arises when a writer is conveying very simple concepts yet attempts to paint them as more sophisticated than they are by using long sentences, usually with repetitive and/ or extraneous language. It never works that way. While you can preclude yourself from properly conveying a concept by using incorrect sentence structure and punctuation, you cannot make your concepts more sophisticated by overreaching. This is not to say that complex concepts require dense and difficult language; certainly a good writer can convey any concept while making it accessible. But it does mean that over-simplifying your language by following an artificial rule regarding "short sentences" will stunt the writing and limit the thinking.

I give her a lot of extra credit for her collection of stories. She has a very special voice. DFW's essays and stories are great but his novels are too dense for me to get any value from in terms of me improving as a writer.

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